The (S)art(re) of Leadership

I manage a website where I have little to no idea what in god’s name I am doing sometimes. I am constantly trying to figure what’s the best way to test user growth, how to manage people, how to teach people to manage themselves, how to manage myself so that I can continually create value.

I look at what I am doing, not just on my website but with many ventures I lack prerequisite knowledge in, as though I am facing a wide and expansive ocean. I am reminded of one of Sartre’s central ideas, that humanity is doomed to be free. I think of all the options before me, of all the things I could do but none which I am certain of, I can’t help but feel on some small level a great fear presiding in the mass of options which I have available to me.

I am not indecisive, nor am hesitant, I am simply uncertain. I lay before an ocean with the only compass being my own convictions, and I feel I must constantly test them, both for myself and for those who are relying on my being correct.

I recognize that no one has any idea what they are doing and that those who feel most confident in where they are going have simply loaned their faith to someone else. There is a hidden existentialism, though I would never say a fear, that I recognize suddenly there is no guide for my actions. I have only myself and my sense of reason to act on, and as much as I hope I shall be correct, hope will deliver no such gifts as an accurate sense of reason.

I see much of management as this. People going into their careers put faith in the idea that “the next guy up” as some semblance of an idea as to what he is doing, who in turn does the same, and so on and so forth, but at the end, no one knows for certain. They are opting on their keenest sense of reason and then praying unreasonably that they are right.

There’s the great wide world before me, a great horde of options for me, and what many fear most is that they will have to choose one. It is easier for most to say that life was meaningless and that their lives were always dictated than to ever fathom that they themselves had control of their lives. I, however, am the man making the decisions, with a team who follows close behind.

I often say that control is the illusion of control. I must be confident in my decision when I have no reason nor notion to be confident in it. I must choose the path before me and walk it, with the fearless as though I knew I was right. But I don’t know I’m right, and the makings of a leader are not so much fearlessness the unknown, as the resistance to the admission of fear.

I, under no circumstance, am certain of my convictions. I must walk them, and lead those behind me, as though I am. I think of the pioneers, who likely had no idea where they were going, but they picked a path and walked it, and let only their own intuition and intelligence guide them.

This is the “Sartre” of managing others. You must look at the whole of the options, and the whole of confusion, and the whole of the reality that you have no idea where to go, and then, before allowing yourself to feel a moment of fear or break in the face of the unknown, to pick a road a trail it to the end of its length. Control is the illusion of control, and leadership is the illusion of leadership, and he who leads, leads by conveying confidence in such a manner that others believe it worth following.

No one in their right mind would hop on a ship with a captain who is not confident of his abilities, or take a road trip with someone who just started driving yesterday, but the man who manages to hide this, and pushes through the anxiety of what lay before him, and put confidence into his own measures and abilities holds the mark of a leader. A leader dispels the idea of fear from the minds of those who follow and dispels doubt from those who would seek to defame. A leader is someone who shields others from fear, either by pushing it away or totally and sufficiently addressing it.

However, everyone must face the “doom of freedom” sooner or later. I am no pessimist and I refuse to view my options as a vice. That said, I had to come to this decision, and seeing the mass of the world you have before you, you will have to come it to. I simply hope you can act as a leader, and looking at the wide ocean before you bravely may you choose a course.